The Highwayman tells the story of a highwayman who is in love with the daughter of an innkeeper. Her name is Bess and she has long black hair and red lips. A jealous ostler (person who works in the stable) who is in love with Bess reports the highwayman to the army.

When they come to ambush him, Bess kills herself to warn him and save his life. When he hears about the way she died, he becomes very angry and is shot down on the highway. The poem ends by saying that the ghosts of the two lovers still meet on nights like the one where we first see them.